This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted by a carboxyl radical, ester, thioester or amide thereof. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g. plant growth regulants and herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may indpendently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA0 when Q is O, then R is H, M, --CH.sub.2 CH.sub.2 OR.sub.7 ; --CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.7, ##STR14## where R.sub.7 is --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, phenyl, --CH.sub.2 CH.sub.2 Cl, --CH.sub.2 CCl.sub.3 ; CH.sub.2 OR.sub.8 ' where R.sub.8 ' is --CH.sub.3, --CH.sub.3 CH.sub.2, --CH(CH.sub.3).sub.2, --CH.sub.2 CH.sub.2 Cl, --CH.sub.2 CCl.sub.3, phenyl, ##STR15## --CH.sub.2 CH.sub.2 OCH.sub.3, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ; --(CH.sub.2 CH.sub.2 O).sub.n' R.sub.8, ##STR16## where R.sub.8 is --CH.sub.3, --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, phenyl, --CH.sub.2 CH.sub.2 Cl, --CH.sub.2 CCl.sub.3 and n' is 2 or 3; ##STR17## where R.sub.12 is --CH.sub.3, --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, or phenyl; and PA0 provided R has a total number of carbon atoms .ltoreq.13; PA0 when Q is ##STR18## then R is hydrogen; C.sub.1 -C.sub.12 alkyl; --(CH.sub.2 CH.sub.2 O)--.sub.n'" R.sub.12 ; --CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.12 where R.sub.12 is as defined above and n"' is 1-3; C.sub.3 -C.sub.10 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.8 cycloalkyl; C.sub.5 -C.sub.6 cycloalkenyl; C.sub.5 -C.sub.8 cycloalkyl substituted with 1 to 3 substituents selected from 0-2 --OCH.sub.3, 0-3 --CH.sub.3 or --C.sub.2 H.sub.5 ; trifluoromethylcyclohexyl; C.sub.4 -C.sub.10 cycloalkylalkyl; C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 --CH.sub.3 ; --CH.sub.2 CN; --CH.sub.2 CH.sub.2 CN; ##STR19## --OCH.sub.3 ; --N(CH.sub.3).sub.2 ; ##STR20## where n, R.sub.9, R.sub.10 and R.sub.11 are as defined above; ##STR21## where R' is hydrogen, C.sub.1 -C.sub.4 alkyl, --OCH.sub.3, F, Br, Cl, --CF.sub.3, CN, NO.sub.2, --SO.sub.2 CH.sub.3, --SCH.sub.3, --N(CH.sub.3).sub.2 ; PA0 R" is hydrogen, C.sub.1 -C.sub.4 alkyl, --OCH.sub.3, F, Br, Cl; PA0 R"' is hydrogen, --CH.sub.3, Cl, F or Br; PA0 R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl, allyl, --CH.sub.2 CN; or --CH.sub.2 CH.sub.2 CN; or R.sub.6 and R can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or ##STR22## with the proviso that when R is --OCH.sub.3 then R.sub.6 is --CH.sub.3 ; when R.sub.6 is --CH.sub.2 CH.sub.2 CN or --CH.sub.2 CN then R is --CH.sub.2 CH.sub.2 CN or CH.sub.2 CN; and R and PA0 R.sub.6 have a total number of carbon atoms .ltoreq.13; PA0 R.sub.1 is ##STR23## R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, --NO.sub.2, --SO.sub.2 CH.sub.3, --OCH.sub.3, --SCH.sub.3, --CF.sub.3, --N(CH.sub.3).sub.2, --NH.sub.2, or --CN; PA0 R.sub.3 is H, Cl, Br, F or CH.sub.3 ; PA0 R.sub.4 is H, or --CH.sub.3 ; PA0 R.sub.5 is H, --CH.sub.3, or --OCH.sub.3 ; PA0 M is an alkali metal; PA0 W is oxygen or sulfur; PA0 X is H, Cl, --CH.sub.3, --OCH.sub.3, --OCH.sub.2 CH.sub.3 or --OCH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 Y is H; F; Cl; Br; C.sub.1 -C.sub.4 alkyl; ##STR24## C.sub.1 -C.sub.4 alkyl substituted with --OCH.sub.3, --OC.sub.2 H.sub.5, --CN, ##STR25## or 1 to 3 atoms of F, Cl, Br; C.sub.3 -C.sub.4 alkenyl; --CH.sub.2 C.tbd.CR.sub.13 where R.sub.13 is H, --CH.sub.3, --CH.sub.2 Cl; --A--(CH.sub.2).sub.n' A.sub.1 --(C.sub.1 -C.sub.3 alkyl), and n', A and A.sub.1 are as previously defined; ##STR26## where L is --NH.sub.2, OH, ##STR27## --NH(C.sub.1 -C.sub.4 alkyl), --N(C.sub.1 -C.sub.4 alkyl).sub.2, C.sub.1 -C.sub.6 alkoxy; SCN; --N.sub.3 ; NR.sub.16 R.sub.17 where R.sub.16 is H or CH.sub.3 and R.sub.17 is H, --OCH.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkyl substituted with --CN, ##STR28## C.sub.3 -C.sub.4 alkenyl; C.sub.3 -C.sub.6 cycloalkyl; or C.sub.2 -C.sub.3 alkyl substituted PA0 with --OCH.sub.3, OC.sub.2 H.sub.5 ; or R.sub.16 and R.sub.17 can be taken together to form --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; --O--R.sub.14 where R.sub.14 is C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br; C.sub.1 -C.sub.4 alkyl substituted with cyano; C.sub.3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.13 ; where R.sub.13 is as previously defined; ##STR29## --SR.sub.15 where R.sub.15 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkyl substituted with CN, allyl, propargyl; with the provision that when Y is .gtoreq.4 carbon atoms, R is .ltoreq.4 carbon atoms, when PA0 Y.sub.1 is H, --OCH.sub.3, --CH.sub.3 or OCH.sub.2 CH.sub.3 ; PA0 X.sub.1 is H, Cl, --OCH.sub.3, --OCH.sub.2 CH.sub.3, --CH.sub.3 ; providing that X.sub.1 and Y.sub.1 are not both simultaneously hydrogen and when R.sub.1 is ##STR30## then R.sub.4 and R.sub.5 are both H and R is .ltoreq.5 carbon atoms. PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfo namide; PA0 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzene sulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzen esulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylb enzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzensulfo namide; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzen esulfonamide, PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbonyl)b enzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbo nyl)benzenesulfonamide; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbon yl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxyc arbonyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-propoxycarbonylb enzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbon yl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-traizin-2-yl)aminocarbonyl]-2-(2-phenyl-1-meth ylethoxycarbonyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[2-(2-chloroetho xy)ethoxycarbonyl]benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-ethoxyethoxyc arbonyl)benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-allyloxycarbonyl benzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-dimethylcarbamoylbenz enesulfonamide; PA0 N-[[[4-methyl-6-(1-methoxycarbonlethoxy)pyrimidin-2-yl]aminocarbonyl]]-2-me thoxycarbonylbenzenesulfonamide; PA0 N-[[[4-methyl-6-(1-methoxycarbonylethoxy)-1,3,5-triazin-2-yl]aminocarbonyl] ]-2-methoxycarbonylbenzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-traizin-2-yl)aminocarbonyl]-2-methylthiocarbon ylbenzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-isopropylthiocar bonylbenzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-isopropylthiocarbonyl benzenesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-traizin-2-yl)aminocarbonyl]-2-(2-methylpropoxy carbonyl)benzensulfonamide. PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(4-morpholinylaminoca rbonyl)benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-pyrrolidinylcarbonyl)be nzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(allyloxycarbonyl)benzenes ulfonamide; PA0 methyl 2-[[[4-(1-carboxyethoxy)-6-methyl-1,3,5-triazin-2-yl]aminocarbonyl]aminosu lfonyl]benzoate; PA0 methyl 2-[[(4-ethoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benz oate; PA0 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N,N-dimethylb enzamide. PA0 Q is O PA0 R is C.sub.1 -C.sub.12 alkyl; C.sub.3 -C.sub.10 alkenyl; C.sub.2 -C.sub.6 alkyl substituted with one or four substituents selected from 0-3 atoms of F, Cl, Br, 0-2 methoxy groups; C.sub.3 -C.sub.6 alkenyl substituted with 1-3 atoms of F, Cl, Br; C.sub.5 -C.sub.8 cycloalkyl; C.sub.5 -C.sub.8 cycloalkenyl; C.sub.5 -C.sub.6 cycloalkyl substituted with any of one to four methyl groups, methoxy, alkyl substituents of C.sub.2 -C.sub.4, F, Cl or Br; C.sub.4 -C.sub.10 cycloalkylalkyl; C.sub.4 -C.sub.8 cycloalkylalkyl with 1-2CH.sub.3 ; --CH.sub.2 CH.sub.2 OR.sub.7 ; CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.7 ; ##STR47## where R.sub.7 is --CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, phenyl, --CHhd 2CH.sub.2 Cl, --CH.sub.2 CCl.sub.3 ; --CH.sub.2 CH.sub.2 O).sub.n R.sub.8 ; ##STR48## where R.sub.8 is CH.sub.3, --CH.sub.2 CH.sub.3 --CH(CH.sub.3).sub.2, phenyl, --CH.sub.2 CH.sub.2 Cl, --CH.sub.2 CCl.sub.3, and n' is 2 or 3; PA0 R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, --NO.sub.2, --OCH.sub.3, --SCH.sub.3, CF.sub.3, SO.sub.2 CH.sub.3, N(CH.sub.3).sub.2, CN; PA0 R.sub.3 is H, Cl, Br or CH.sub.3
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl, or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959]: ##STR7## wherein R=H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.